The Hardest Conversation to Have with a Founder

The most fun part about being an Executive Coach is working with really smart, ambitious Founders who are succeeding, but know they can do even more by upping their game.

The second most fun is working with Founders who are having some degree of success but know they are falling behind their competitors.

The hardest conversations, though, are with those Founders who have waited too long to get help. Whether it was “being too busy” to get coaching, pride (“I don’t need that”) or an unwillingness to invest in increasing their likelihood of success, these sessions are very different than the first two. Sometimes they sign-up directly; other times they are “urged” by their VC’s or Board Members to get help.

Often on the verge of burnout and knowing their runway is shrinking, they engage me with hopes that in several months I can fix the things they failed to do during the past several years.

About 30% of the time, our work leads them to salvage what they started and get back on the pathway to success. But in the other 70%, we engage in very difficult discussions which often lead them to the realization that no matter what they do, they have lost the race. I hate those discussions, but as a professional, I am obligated to try to help them find a way.

As a coach, what I find so sad is that many of those in that third group were just as smart, ambitious and had as great an idea as their competitors. Had they come to me sooner, we could have helped ensure they emerged a winner. But they waited too long and those talks then shift to helping the Founder understand what went wrong, why and how to avoid making the same mistakes in their next venture (avoiding the dreaded “getting a job”).

If you’re in that third group, there’s still a one in three chance I can help you. But for those of you in the first two groups, let’s talk before you end up being part of group three.

stevegoldin@proptechcoaching.com